Basic information
- Standard SMILES
COS(=O)(=O)[O-].C[n+]1c2ccccc2nc2ccccc21- InChIKey
RXGJTUSBYWCRBK-UHFFFAOYSA-M- Molecular formula
- C14H14N2O4S
- Average molar mass
- 306.34 g/mol
- Monoisotopic mass
- 306.06742793
Overview
5-methylphenazinium methyl sulfate is an azaheterocycle sulfate salt and a member of phenazines.
Names & identifiers
- Preferred name
- Phenazine Methosulfate
- IUPAC
- 5-methylphenazin-5-ium;methyl sulfate
- English name
- Phenazine methosulfate
- Molecular formula
- C14H14N2O4S
- Molecular weight
- 306.34
Names & synonyms
Phenazine methosulfate299-11-65-Methylphenazinium methyl sulfateN-Methylphenazonium methosulfatePhenazine methosulphateMethylphenazonium methosulfate5-Methylphenazine methylsulfateN-Methylphenazinium methosulfateN-Methylphenazonium methosulphatePMS (pharmaceutical)Phenazinium, 5-methyl-, methyl sulfate5-Methyl phenazine, methyl sulfate salt
Show more names
PMSPHENAZINE METHYL SULFATEPhenazine methosuL5-MethylphenaziniumPhenazine methosulfaPhezine methosulfatePhenazine MethoshlphatePHENAZINE METHOLSULPHATE
J3GYQ3401YDTXSID1059783NSC-34661CHEBI:8055Methosulfate, PhenazineMethosulfate, Methylphenazonium5 Methylphenazinium Methyl SulfateMethyl Sulfate, 5-Methylphenazinium
Database identifiers
- CAS
299-11-6- PubChem CID
- 9285
- DTXSID
DTXSID1059783- ChEBI
CHEBI:8055- UNII
- J3GYQ3401Y
- EC Number
- 206-072-1
Properties
Computed structural properties
- Topological polar surface area
- 91.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 297
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
Physical DescriptionYellow to brown solid; [Merck Index] Yellow crystalline solid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 158 · 158-160 °C (dec.)(lit.)
- Density
- 1.3395 · 1.3395 (rough estimate)
- refractive index
- 1.693 · 1.6930 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- 2 O: · H2O: 0.2 g/mL at 20 °C, clear, deep orange
- form
- Crystalline Powder
- color
- Dark yellow to brown or khaki
- Water Solubility
- soluble in water (approximately 200 mg/ml).
- Sensitive
- Light Sensitive
- Merck
- 14 · 14,6109
- BRN
- 3898869 · 3898869
- Stability
- Stable. Incompatible with strong oxidizing agents.
- InChI
- InChI=1S/C13H11N2.CH4O4S/c1-15-12-8-4-2-6-10(12)14-11-7-3-5-9-13(11)15;1-5-6(2,3)4/h2-9H,1H3;1H3,(H,2,3,4)/q+1;/p-1
- InChIKey
- RXGJTUSBYWCRBK-UHFFFAOYSA-M
- SMILES
- C12C=CC=CC1=NC1=CC=CC=C1[N+]=2C.S([O-])(=O)(=O)OC
- CAS DataBase Reference
- 299 · 299-11-6(CAS DataBase Reference)
- FDA UNII
- 3 GYQ3401Y · J3GYQ3401Y
- EPA Substance Registry System
- 5 · Phenazinium, 5-methyl-, methyl sulfate (299-11-6)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn,T
- Risk Statements
- 36 · 36/37/38-68-46
- Safety Statements
- 26 · 26-36/37/39-53-45
- RIDADR
- 2811 · 2811
- WGK Germany
- 3 · 3
- RTECS
- 1645000 · SG1645000
- F
- 8 · 8
- TSCA
- TSCA listed
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationPhenazinium, 5-methyl-, methyl sulfate: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA moderate irritant; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- F
- 8
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SG1645000
- ridadr
- 2811
- hs_code
- 29339900
- risk_code
- 36/37/38-68-46
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn,T
- safety_code
- 26-36/37/39-53-45
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Uses & manufacturing
UsesUsed as an electron carrier and to make succinic dehydrogenase; [Merck Index]
General Manufacturing InformationPhenazinium, 5-methyl-, methyl sulfate (1:1): INACTIVE
Applications
DescriptionPhenazine is a free radical generator. It has been used as an electron transfer reactant in cell viability assays. Phenazine (10 μM) induces ssDNA break formation in the presence of the reducing agent NADPH in a cell-free plasmid cleavage assay when used at a concentration of 10 μM. It induces oxidative DNA damage in an alkaline comet assay and apoptosis in A375 melanoma cells when used at a concentration of 10 μM. Phenazine (20 nM) oxidizes cysteine-containing proteins in HepG2 cells.
UsesPhenazine Methosulfate is used in tyrosine transaminase test and for enzymic determination of ethanol in blood by the colorimetric micromethod. Used with ascorbic acid to determine nitric oxide reductase activity. Since the reduced PMS is easily oxidized by oxygen, it is used in assays as an electron carrier between enzymes and oxygen, cytochrome c, indophenols, or tetrazolium salts. The reduced PMS is used as an electron donor to reduce cytochrome c or in photosynthetic experiments. Usage of PMS for detection of specific dehydrogenases has been reported.
General DescriptionPhenazines are heterocyclic compounds produced as secondary metabolites by bacteria.
Upstream & downstream products
Upstream raw materials
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Additional notes
DefinitionChEBI: 5-methylphenazinium methyl sulfate is an azaheterocycle sulfate salt and a member of phenazines. It is used as an electron carrier in place of the flavine enzyme of Warburg in the hexosemonophosphate system and also in the preparation of succinic dehydrogenase. Green et al., J. Biol. Chem. 217, 551 (1955).
Related reactions
6 records
Linked notes
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